supplementary materials

The title compound, [Ni(C60H52N4)], is an example of a meso tetrasubstituted nickel(II) porphyrin with both meso aryl and alkyl residues. The molecule exhibits a planar macrocycle with an average deviation of the 24 macrocycle atoms from their least-squares plane (24) of 0.01 Å and an average Ni-N bond length of 1.960 (2) Å. The NiII atom lies on a center of inversion. The structure presents a rare example for a planar nickel(II) porphyrin, as meso-substituted nickel(II) porphyrins with either only meso-aryl or with meso-alkyl residues typically exhibit a ruffled conformation.

In continuation of studies on the conformational flexibility of porphyrins
(Senge, 2006) the structure of the title compound was determined as an
example
for a meso substituted porphyrin with both meso alkyl and
meso aryl subsitutents (Senge et al., 2010) and in
relation to
current synthetic studies on anthracenyl porphyrins (Volz & Schäffer,
1985;
Davis et al., 2008; Sooambar et al., 2009).

The structure of (I), is shown in Fig. 1. The molecule exhibits a completely
planar macrocycle with an average deviation of the 24 macrocycle atoms from
their least-squares-plane (Δ24) of 0.01 Å and an average Ni—N bond length
of 1.960 (2) Å. All geometrical parameters are typical for a planar
nickel(II) porphyrin (Senge et al., 2000). No individual
macrocycle
atom was displaced more then 0.015 Å from the mean plane. Likewise,
differences in bond angles and lenghts between the meso aryl and
meso alkyl quadrants are minimal. The anthracenyl residues are almost
orthogonal to the plane of the four nitrogen atoms (96.2°) similarly to the
situation found in related zinc(II) systems with meso aryl residues
(Sooambar et al., 2009). In the crystal packing there are no
close
contacts (not shown). The anthracene residues prevent π-stacking of the
porphyrins and the hexyl side chains are oriented between neighboring
anthracenyl substituents and hinder π-stacking as well.

The compound was prepared via metallation of the respective free base
porphyrin and crystallized via liquid diffusion of methanol into a
solution of the porphyrin in methylene chloride. Crystals were handled as
described by Hope (1994).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.